Zen and the Art of Real Estate Investing with Jonathan Greene

120: Financial Independence Through Design and Architecture with Diana Ossa & Josh Dobken


A W-2 position to back you up as you begin your real estate investing career is a great way to establish stability and a steady income. It’s even better if your W-2 career happens to be real estate adjacent.

On this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Diana Ossa and Josh Dobken to the show. Diana and Josh are architects, designers, construction managers, real estate investors, and mid-term rental hosts. Their complementary strengths have led to an investing venture that continues to grow as Diana and Josh work toward their goals together.

Jonathan, Diana, and Josh start their conversation by exploring their backgrounds as architects, Diana’s focus on studio art and construction management, and Josh’s emphasis on construction management and hospitality. You’ll hear them explain the challenges of a limited budget on large-scale projects in terms of architectural design, what pushed them both toward real estate investing careers while maintaining their W-2 positions, and how they landed on Kansas City for their initial investment. Diana and Josh share why they pivoted toward commercial real estate, the great deal that almost was and why it fell through, and how they decided why no deal is better than a bad deal. Finally, Jonathan, Diana, and Josh cover hospitality’s role in property management and cohosting in mid-term rentals, where their business is going in the future with a boutique hotel in their sights, and their reasons for keeping the scale small to remain in the boutique world and staffing manageable.

While architecture may not be the first profession to come to mind when you think of real estate investors, Diana Ossa and Josh Dobken are proving that architects have precisely what it takes to be great investors.

In this episode, you will hear:

  • Diana Ossa and Josh Dobken’s backgrounds and how they complement one another
  • How a limited budget on a large-scale project can present challenges in architectural design
  • The catalysts that pushed Diana and Josh to begin their real estate investing careers and their “why” behind it
  • The biggest gift real estate gave Diana and why she is no longer willing to sacrifice everything for a W-2 architecture career
  • Why Josh does not plan to leave his W-2 and the stability it provides to continue pursuing real estate investing
  • The markets Diana and Josh explored for their first property and how relocating to Kansas City ended up being a fantastic decision
  • Their pivot to commercial real estate and its appeal to Diana and Josh with their architectural backgrounds
  • The property they found just outside Rocky Mountain National Park that they acted quickly on and the reasons the deal fell through
  • Why no deal is better than a bad deal—even if you can force the numbers
  • Hospitality’s role in property management and cohosting with others in mid-term rentals
  • Where Diana and Josh’s business is going over the next couple of years, with a boutique hotel at the forefront
  • Keeping the scale small for the boutique world and staffing needs

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